NP-MRD: Showing NP-Card for eupachinin A (NP0042555)

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Record Information

Version

2.0

Created at

2021-06-21 00:11:07 UTC

Updated at

2021-06-30 00:17:42 UTC

NP-MRD ID

NP0042555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eupachinin A

Provided By

JEOL Database JEOL Logo

Description

(+)-Eupachinin A belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. eupachinin A is found in Eupatorium chinense. eupachinin A was first documented in 2013 (Wang, W.-J., et al.). Based on a literature review very few articles have been published on (+)-Eupachinin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102113D          

 34 36  0  0  0  0            999 V2000
   -5.2754   -2.8217    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9806   -2.7232    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8326   -3.0045   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -2.2759   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.9396    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691   -1.5206    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -1.1178    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.8229   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251   -1.0390   -1.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.4567   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -1.7800   -2.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -2.1903   -1.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746   -2.5018   -2.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.3610   -0.3093 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5145    0.6181   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -1.5292   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.2607    1.0939 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7506   -0.6228    2.2239 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2808   -0.9876    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -1.2078    2.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3048   -3.1678    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833   -1.8400    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093   -3.5481    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.9910    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947   -1.7172   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -2.7746   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    0.1590   -2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    1.5167   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.9221   -1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.9389   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    0.4224    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8234    1.2397    1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.5554    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.0875    3.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6 10  2  0  0  0  0
 12 11  2  0  0  0  0
  7 19  1  0  0  0  0
  8 14  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 10  1  0  0  0  0
  4  2  1  0  0  0  0
 10  9  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
  2  3  2  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
  7  8  2  0  0  0  0
 14 16  1  1  0  0  0
  4 12  1  0  0  0  0
 14 15  1  0  0  0  0
  6  5  1  0  0  0  0
 19 20  2  0  0  0  0
 11 25  1  0  0  0  0
  5 24  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
 13 26  1  0  0  0  0
 16 30  1  0  0  0  0
 15 27  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.2754   -2.8217    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9806   -2.7232    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8326   -3.0045   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -2.2759   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.9396    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691   -1.5206    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -1.1178    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.8229   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251   -1.0390   -1.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.4567   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -1.7800   -2.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -2.1903   -1.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746   -2.5018   -2.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.3610   -0.3093 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5145    0.6181   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -1.5292   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.2607    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.6228    2.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808   -0.9876    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -1.2078    2.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3048   -3.1678    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833   -1.8400    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093   -3.5481    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.9910    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947   -1.7172   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -2.7746   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    0.1590   -2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    1.5167   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.9221   -1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.9389   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    0.4224    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8234    1.2397    1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.5554    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.0875    3.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  6 10  2  0
 12 11  2  0
  7 19  1  0
  8 14  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 11 10  1  0
  4  2  1  0
 10  9  1  0
  2  1  1  0
  9  8  1  0
  2  3  2  0
  7  6  1  0
 12 13  1  0
  7  8  2  0
 14 16  1  1
  4 12  1  0
 14 15  1  0
  6  5  1  0
 19 20  2  0
 11 25  1  0
  5 24  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 13 26  1  0
 16 30  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END


  Mrv1652306212102113D          

 34 36  0  0  0  0            999 V2000
   -5.2754   -2.8217    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9806   -2.7232    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8326   -3.0045   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -2.2759   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.9396    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691   -1.5206    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -1.1178    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.8229   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251   -1.0390   -1.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.4567   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -1.7800   -2.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -2.1903   -1.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746   -2.5018   -2.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.3610   -0.3093 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5145    0.6181   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -1.5292   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.2607    1.0939 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7506   -0.6228    2.2239 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2808   -0.9876    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -1.2078    2.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3048   -3.1678    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833   -1.8400    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093   -3.5481    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.9910    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947   -1.7172   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -2.7746   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    0.1590   -2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    1.5167   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.9221   -1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.9389   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    0.4224    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8234    1.2397    1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.5554    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.0875    3.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6 10  2  0  0  0  0
 12 11  2  0  0  0  0
  7 19  1  0  0  0  0
  8 14  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 10  1  0  0  0  0
  4  2  1  0  0  0  0
 10  9  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
  2  3  2  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
  7  8  2  0  0  0  0
 14 16  1  1  0  0  0
  4 12  1  0  0  0  0
 14 15  1  0  0  0  0
  6  5  1  0  0  0  0
 19 20  2  0  0  0  0
 11 25  1  0  0  0  0
  5 24  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
 13 26  1  0  0  0  0
 16 30  1  0  0  0  0
 15 27  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042555

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1C(=O)C([H])([H])[H])C1=C(O2)[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-7(16)8-5-9-12(6-11(8)18)20-14-13(9)10(17)3-4-15(14,2)19/h5-6,18-19H,3-4H2,1-2H3/t15-/m1/s1

> <INCHI_KEY>
GAMROFBVEMOBPH-OAHLLOKOSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.272

> <EXACT_MASS>
274.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.207354111467627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-12-acetyl-6,11-dihydroxy-6-methyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),10,12-tetraen-3-one

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
1.3140969909999998

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.866857839458163

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.373390365905045

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0574433764512023

> <JCHEM_POLAR_SURFACE_AREA>
87.74000000000001

> <JCHEM_REFRACTIVITY>
71.5827

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-12-acetyl-6,11-dihydroxy-6-methyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),10,12-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.2754   -2.8217    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9806   -2.7232    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8326   -3.0045   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -2.2759   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.9396    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691   -1.5206    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -1.1178    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.8229   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251   -1.0390   -1.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.4567   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -1.7800   -2.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -2.1903   -1.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746   -2.5018   -2.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.3610   -0.3093 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5145    0.6181   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -1.5292   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.2607    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.6228    2.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808   -0.9876    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -1.2078    2.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3048   -3.1678    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833   -1.8400    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093   -3.5481    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.9910    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947   -1.7172   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -2.7746   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    0.1590   -2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    1.5167   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.9221   -1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.9389   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    0.4224    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8234    1.2397    1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.5554    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.0875    3.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  6 10  2  0
 12 11  2  0
  7 19  1  0
  8 14  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 11 10  1  0
  4  2  1  0
 10  9  1  0
  2  1  1  0
  9  8  1  0
  2  3  2  0
  7  6  1  0
 12 13  1  0
  7  8  2  0
 14 16  1  1
  4 12  1  0
 14 15  1  0
  6  5  1  0
 19 20  2  0
 11 25  1  0
  5 24  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 13 26  1  0
 16 30  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.275  -2.822   1.492  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.981  -2.723   0.019  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.833  -3.005  -0.825  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.630  -2.276  -0.437  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.632  -1.940   0.497  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.369  -1.521   0.032  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.149  -1.118   0.631  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.710  -0.823  -0.403  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.125  -1.039  -1.607  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.148  -1.457  -1.343  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.104  -1.780  -2.298  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.351  -2.190  -1.815  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.275  -2.502  -2.783  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.120  -0.361  -0.309  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.515   0.618  -1.408  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.930  -1.529  -0.400  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.320   0.261   1.094  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.751  -0.623   2.224  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.281  -0.988   2.008  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.478  -1.208   2.949  0.00  0.00           O+0
HETATM   21  H   UNK     0      -6.305  -3.168   1.629  0.00  0.00           H+0
HETATM   22  H   UNK     0      -5.183  -1.840   1.964  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.609  -3.548   1.965  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.798  -1.991   1.569  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.895  -1.717  -3.359  0.00  0.00           H+0
HETATM   26  H   UNK     0      -5.108  -2.775  -2.334  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.429   0.159  -2.400  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.888   1.517  -1.395  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.562   0.922  -1.299  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.739  -1.939  -1.264  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.388   0.422   1.285  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.823   1.240   1.138  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.320  -1.555   2.305  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.836  -0.088   3.176  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2   12                                                  
CONECT    5    4    6   24                                                  
CONECT    6   10    7    5                                                  
CONECT    7   19    6    8                                                  
CONECT    8   14    9    7                                                  
CONECT    9   10    8                                                       
CONECT   10    6   11    9                                                  
CONECT   11   12   10   25                                                  
CONECT   12   11   13    4                                                  
CONECT   13   12   26                                                       
CONECT   14    8   17   16   15                                             
CONECT   15   14   27   28   29                                             
CONECT   16   14   30                                                       
CONECT   17   14   18   31   32                                             
CONECT   18   17   19   33   34                                             
CONECT   19    7   18   20                                                  
CONECT   20   19                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    5                                                            
CONECT   25   11                                                            
CONECT   26   13                                                            
CONECT   27   15                                                            
CONECT   28   15                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
   -5.2754   -2.8217    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9806   -2.7232    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8326   -3.0045   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -2.2759   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.9396    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691   -1.5206    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -1.1178    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.8229   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251   -1.0390   -1.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481   -1.4567   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -1.7800   -2.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -2.1903   -1.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746   -2.5018   -2.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.3610   -0.3093 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5145    0.6181   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -1.5292   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.2607    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.6228    2.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808   -0.9876    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -1.2078    2.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3048   -3.1678    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833   -1.8400    1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093   -3.5481    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -1.9910    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947   -1.7172   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -2.7746   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    0.1590   -2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    1.5167   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.9221   -1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.9389   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    0.4224    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8234    1.2397    1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.5554    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.0875    3.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  6 10  2  0
 12 11  2  0
  7 19  1  0
  8 14  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 11 10  1  0
  4  2  1  0
 10  9  1  0
  2  1  1  0
  9  8  1  0
  2  3  2  0
  7  6  1  0
 12 13  1  0
  7  8  2  0
 14 16  1  1
  4 12  1  0
 14 15  1  0
  6  5  1  0
 19 20  2  0
 11 25  1  0
  5 24  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 13 26  1  0
 16 30  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2720 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

(6R)-12-acetyl-6,11-dihydroxy-6-methyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),10,12-tetraen-3-one

Traditional Name

(6R)-12-acetyl-6,11-dihydroxy-6-methyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),10,12-tetraen-3-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1C(=O)C([H])([H])[H])C1=C(O2)[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C1=O

InChI Identifier

InChI=1S/C15H14O5/c1-7(16)8-5-9-12(6-11(8)18)20-14-13(9)10(17)3-4-15(14,2)19/h5-6,18-19H,3-4H2,1-2H3/t15-/m1/s1

InChI Key

GAMROFBVEMOBPH-OAHLLOKOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eupatorium chinense	JEOL database	Wang, W.-J., et al, Tetrahedron Lett. 54, 3321 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Acetophenone
Benzofuran
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Furan
Tertiary alcohol
Heteroaromatic compound
Vinylogous acid
Ketone
Oxacycle
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.19	ALOGPS
logP	1.31	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.37	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.74 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.58 m³·mol⁻¹	ChemAxon
Polarizability	28.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102443326

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, W.-J., et al. (2013). Wang, W.-J., et al, Tetrahedron Lett. 54, 3321 (2013). Tetrahedron Lett.

Showing NP-Card for eupachinin A (NP0042555)

MOL for NP0042555 (eupachinin A)

3D MOL for NP0042555 (eupachinin A)

3D SDF for NP0042555 (eupachinin A)

3D-SDF for NP0042555 (eupachinin A)

PDB for NP0042555 (eupachinin A)

3D PDB for NP0042555 (eupachinin A)

SMILES for NP0042555 (eupachinin A)

INCHI for NP0042555 (eupachinin A)

Structure for NP0042555 (eupachinin A)

3D Structure for NP0042555 (eupachinin A)